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US4110355A Expired / Lapsed US ⏱️ 0.0 years remaining

Anthraquinone compounds useful in photographic processes

Assignee: Polaroid Corp
•
Filing: 1973-05-23
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Granted: 1978-08-29
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Expires: 1993-05-23
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Abstract

Abstract This invention relates to a novel class of compounds which are capable of reacting in such a way as to form a new heterocyclic ring, and as a function of such reaction and ring formation to split off a color-providing material.

Inventors

  • 👤 Stanley M. Bloom

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-01 03:02
CPC Classifications
G; G03; G03C; G03C8/00; G03C8/02; G03C8/08; G03C8/10; C; C09; C09B; C09B1/00; C09B1/02; C09B1/06; C09B1/16; C09B1/20; C09B1/26; C09B1/28; C09B1/50; C09B1/503; C09B1/51; C09B1/515; C09B1/54; C09B1/545; C09B29/00; C09B29/0003; C09B29/10; C09B29/34; C09B29/36; C09B29/3604; C09B29/3647; C09B29/3652; C09B29/3656; C09B31/00; C09B31/02; C09B31/08; C09B45/00; C09B45/02; C09B45/14; C09B45/16

Claims Analysis

Total Claims: 19
Claim 1
Independent Claim 274 words
A compound of the formula ##STR49## wherein: A represents the atoms necessary to complete a benzene or naphthalene radical; D is an anthraquinone dye moiety; Z 1 is hydrogen or a substituent replaceable by an oxidized aromatic amino color developer in elimination-coupling reactions; said substituent being selected from the group consisting of chloro, bromo, carboxy, sulfo, hydroxy, alkoxy and hydroxyalkyl; Y is the residue of an acid forming an amide with and reducing the basic character of the nitrogen atom to which it is bonded and is selected from the group consisting ##STR50## X 1 is hydroxy or a primary, secondary or tertiary amino of the formula ##STR51## wherein each R 3 is hydrogen, alkyl, phenyl, naphthyl, or each R 3 may be alkylene so that the R 3 's together with the nitrogen atom provide a heterocyclic ring having 5 or 6 carbon atoms or each R 3 may be a lower alkyl having a substituent chosen from the group consisting of a hydroxy substituent, a methoxyethoxy substituent, a polyglycoloxy substituent, a carboxy substituent, an ethoxycarboxy substituent, a benzyl substituent, a phenyl substituent, a sulfo-phenyl substituent, an acetylaminophenyl substituent, a succinylaminophenyl substituent or a furane substituent; R is an anchoring substituent rendering the compound non diffusible said substituent containing a higher alkyl radical bonded to a single carbon atom of said aromatic nucleus formed by said A moiety; R 1 is hydrogen or alkyl; and n is 2 or n may be 1 when X 1 is a secondary or tertiary amino comprising an anchoring moiety rendering said compound non diffusible or R 1 is an alkyl radical providing such an anchoring moiety.
Claim 2
Dependent Claim 274 words
A compound of the formula ##STR49## wherein: A represents the atoms necessary to complete a benzene or naphthalene radical; D is an anthraquinone dye moiety; Z 1 is hydrogen or a substituent replaceable by an oxidized aromatic amino color developer in elimination-coupling reactions; said substituent being selected from the group consisting of chloro, bromo, carboxy, sulfo, hydroxy, alkoxy and hydroxyalkyl; Y is the residue of an acid forming an amide with and reducing the basic character of the nitrogen atom to which it is bonded and is selected from the group consisting ##STR50## X 1 is hydroxy or a primary, secondary or tertiary amino of the formula ##STR51## wherein each R 3 is hydrogen, alkyl, phenyl, naphthyl, or each R 3 may be alkylene so that the R 3 's together with the nitrogen atom provide a heterocyclic ring having 5 or 6 carbon atoms or each R 3 may be a lower alkyl having a substituent chosen from the group consisting of a hydroxy substituent, a methoxyethoxy substituent, a polyglycoloxy substituent, a carboxy substituent, an ethoxycarboxy substituent, a benzyl substituent, a phenyl substituent, a sulfo-phenyl substituent, an acetylaminophenyl substituent, a succinylaminophenyl substituent or a furane substituent; R is an anchoring substituent rendering the compound non diffusible said substituent containing a higher alkyl radical bonded to a single carbon atom of said aromatic nucleus formed by said A moiety; R 1 is hydrogen or alkyl; and n is 2 or n may be 1 when X 1 is a secondary or tertiary amino comprising an anchoring moiety rendering said compound non diffusible or R 1 is an alkyl radical providing such an anchoring moiety.
Claim 3
Dependent Claim 16 words
A compound as defined in claim 1 wherein R 1 is hydrogen, and n is 2.
Claim 4
Dependent Claim 25 words
A compound as defined in claim 1 wherein R comprises a higher alkyl linked directly to said aromatic nucleus or indirectly through a --CONH-- substituent.
Claim 5
Dependent Claim 312 words
A compound of the formula ##STR52## wherein: each of A and A 1 represents the atoms necessary to complete a benzene or naphthalene radical; D is an anthraquinone dye moiety; Y is the residue of an acid forming an amide with and reducing the basic character of the nitrogen atom to which it is bonded and is selected from the group consisting ##STR53## X and X 2 each is the substituent R, hydrogen, hydroxy, a primary, secondary or tertiary amino of the formula ##STR54## wherein each R 3 is hydrogen, alkyl, phenyl, naphthyl, or each R 3 may be alkylene so that the R 3 's together with the nitrogen atom provide a heterocyclic ring having 5 or 6 carbon atoms or each R 3 may be a lower alkyl having a substituent chosen from the group consisting of a hydroxy substituent, a methoxyethoxy substituent, a polyglycoloxy substituent, a carboxy substituent, an ethoxycarboxy substituent, a benzyl substituent, a phenyl substituent, a sulfo-phenyl substituent, an acetylaminophenyl substituent, a succinylaminophenyl substituent or a furane substituent provided that at least one of X and X 2 must be hydroxy or amino; R and R 4 each represent an anchoring substituent rendering the compound non diffusible, said substituent containing a higher alkyl radical bonded to a single carbon atom of said aromatic nucleus formed by said A or A 1 moieties respectively; R 1 is hydrogen or alky; and n and n 1 each is 1 or 2 and each n and n 1 may be 1 when one X or X 2 is the substituent R or a secondary or tertiary amino comprising an anchoring moiety rendering the compound non diffusible or when R 1 is an alkyl substituent providing such an anchoring moiety but when said substituents do not contribute an anchoring moiety, at least one of n and n 1 must be 2.
Claim 6
Dependent Claim 312 words
A compound of the formula ##STR52## wherein: each of A and A 1 represents the atoms necessary to complete a benzene or naphthalene radical; D is an anthraquinone dye moiety; Y is the residue of an acid forming an amide with and reducing the basic character of the nitrogen atom to which it is bonded and is selected from the group consisting ##STR53## X and X 2 each is the substituent R, hydrogen, hydroxy, a primary, secondary or tertiary amino of the formula ##STR54## wherein each R 3 is hydrogen, alkyl, phenyl, naphthyl, or each R 3 may be alkylene so that the R 3 's together with the nitrogen atom provide a heterocyclic ring having 5 or 6 carbon atoms or each R 3 may be a lower alkyl having a substituent chosen from the group consisting of a hydroxy substituent, a methoxyethoxy substituent, a polyglycoloxy substituent, a carboxy substituent, an ethoxycarboxy substituent, a benzyl substituent, a phenyl substituent, a sulfo-phenyl substituent, an acetylaminophenyl substituent, a succinylaminophenyl substituent or a furane substituent provided that at least one of X and X 2 must be hydroxy or amino; R and R 4 each represent an anchoring substituent rendering the compound non diffusible, said substituent containing a higher alkyl radical bonded to a single carbon atom of said aromatic nucleus formed by said A or A 1 moieties respectively; R 1 is hydrogen or alky; and n and n 1 each is 1 or 2 and each n and n 1 may be 1 when one X or X 2 is the substituent R or a secondary or tertiary amino comprising an anchoring moiety rendering the compound non diffusible or when R 1 is an alkyl substituent providing such an anchoring moiety but when said substituents do not contribute an anchoring moiety, at least one of n and n 1 must be 2.
Claim 7
Dependent Claim 30 words
A compound as defined in claim 4 wherein each of R and R 4 comprises a higher alkyl linked directly to said aromatic nucleus or indirectly through a --CONH-- substituent.
Claim 8
Dependent Claim 76 words
A compound of the formula: ##STR55## wherein: each of R and R 4 comprises an amide of at least 13 carbon atoms, said amide being bonded directly to a nuclear carbon atom of the shown benzene moiety or linked thereto through a phenylene or alkylene substituent; each of n and n 1 is 1 or 2 provided that at least one of said n and n 1 is 2; and D is an anthraquinone dye moiety.
Claim 9
Dependent Claim 76 words
A compound of the formula: ##STR55## wherein: each of R and R 4 comprises an amide of at least 13 carbon atoms, said amide being bonded directly to a nuclear carbon atom of the shown benzene moiety or linked thereto through a phenylene or alkylene substituent; each of n and n 1 is 1 or 2 provided that at least one of said n and n 1 is 2; and D is an anthraquinone dye moiety.
Claim 10
Dependent Claim 96 words
A compound of the formula: ##STR56## wherein: D is an anthraquinone dye moiety; Z 1 is hydrogen or a substituent replaceable by oxidized aromatic amino color developer in elimination-coupling reactions, said substituent being chloro, bromo, carboxy, sulfo, hydroxy, alkxoy or hydroxyalkyl; R 1 is hydrogen or alkyl; X 1 is hydroxy or amino; R is an anchoring moiety which renders the compound nondiffusible and comprises a higher alkyl of at least 10 carbon atoms bonded to a nuclear carbon atom of the shown benzene moiety by a linking group which is --CONH--; and n is 2.
Claim 11
Dependent Claim 96 words
A compound of the formula: ##STR56## wherein: D is an anthraquinone dye moiety; Z 1 is hydrogen or a substituent replaceable by oxidized aromatic amino color developer in elimination-coupling reactions, said substituent being chloro, bromo, carboxy, sulfo, hydroxy, alkxoy or hydroxyalkyl; R 1 is hydrogen or alkyl; X 1 is hydroxy or amino; R is an anchoring moiety which renders the compound nondiffusible and comprises a higher alkyl of at least 10 carbon atoms bonded to a nuclear carbon atom of the shown benzene moiety by a linking group which is --CONH--; and n is 2.
Claim 12
Dependent Claim 108 words
A compound of the formula: ##STR57## wherein: D is an anthraquinone dye moiety; R 1 is hydrogen; one of X 1 or X 2 is hydroxy or amino and the other is hydrogen or the substituent R; each R is an anchoring moiety rendering the compound nondiffusible and comprises a higher alkyl of at least 10 carbon atoms bonded to a nuclear carbon atom of the shown benzene moiety by a linking group which is --CONH--; and one of n and n 1 is 2 and the other is 1 unless X 1 or X 2 is R, in which case both n and n 1 are 1.
Claim 13
Dependent Claim 108 words
A compound of the formula: ##STR57## wherein: D is an anthraquinone dye moiety; R 1 is hydrogen; one of X 1 or X 2 is hydroxy or amino and the other is hydrogen or the substituent R; each R is an anchoring moiety rendering the compound nondiffusible and comprises a higher alkyl of at least 10 carbon atoms bonded to a nuclear carbon atom of the shown benzene moiety by a linking group which is --CONH--; and one of n and n 1 is 2 and the other is 1 unless X 1 or X 2 is R, in which case both n and n 1 are 1.
Claim 14
Dependent Claim 3 words
The compound: ##STR58##
Claim 15
Dependent Claim 3 words
The compound: ##STR58##
Claim 16
Dependent Claim 3 words
The compound: ##STR59##
Claim 17
Dependent Claim 3 words
The compound: ##STR59##
Claim 18
Dependent Claim 3 words
The compound: ##STR60##
Claim 19
Dependent Claim 3 words
The compound: ##STR60##

References Cited (Backward Citations)

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USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1981-08-28 1982-02-27 1982-08-29 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1985-08-28 1986-02-27 1986-08-29 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1989-08-28 1990-02-27 1990-08-29 $7700.00 Window Closed / Lapsed

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